[ CAS No. 134756-75-5 ]

Name: 134756-75-5|(S)-2-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidine|97%
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Quality Control of [ 134756-75-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 134756-75-5 ]

CAS No. :	134756-75-5	MDL No. :	MFCD11502840
Formula :	C₁₁H₂₅NOSi	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	215.41 g/mol	Pubchem ID :	11275950
Synonyms :

Calculated chemistry of of [ 134756-75-5 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	68.55
TPSA :	21.26 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.32
Log Po/w (XLOGP3) :	2.99
Log Po/w (WLOGP) :	2.38
Log Po/w (MLOGP) :	1.81
Log Po/w (SILICOS-IT) :	1.05
Consensus Log Po/w :	2.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.8
Solubility :	0.345 mg/ml ; 0.0016 mol/l
Class :	Soluble
Log S (Ali) :	-3.1
Solubility :	0.171 mg/ml ; 0.000794 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.05
Solubility :	0.192 mg/ml ; 0.000889 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.09

Safety of [ 134756-75-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 134756-75-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 134756-75-5 ]
Downstream synthetic route of [ 134756-75-5 ]

[ 134756-75-5 ] Synthesis Path-Upstream 1~4

1
[ 18162-48-6 ]
[ 23356-96-9 ]
[ 134756-75-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In dichloromethane at 20℃;	To a solution of (S)-pyrrolidin-2-yl-methanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0° C. was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH₄Cl (20 mL). The aqueous layer was extracted with DCM (2×50 mL). Combined organics were washed with brine, dried over Na₂SO₄, filtered and evaporated to dryness to give the title compound (1.11 g, 76percent) as a yellow oil. MS: 216.2 (M+H⁺)
76%	With triethylamine In dichloromethane at 0 - 20℃;	Intermediate A-36-{5-[(S)-2-(tei"i-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-l-yl]-pyridin-3-yl}-l- methyl-3,4-dihydro-lH-quinolin-2-one [A] (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidineTo a solution of (S)-pyrrolidin-2-yl-methanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 °C was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH₄C1 (20 mL). The aqueous layer was extracted with DCM (2 x 50 mL). Combined organics were washed with brine, dried over Na₂S0₄, filtered and evaporated to dryness to give the title compound (1.11 g, 76percent) as a yellow oil. MS: 216.2 (M+H⁺).
76%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere	To a solution of (S)-pyrrolidin-2-ylmethanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 °C was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH₄C1 (20 mL). The aqueous layer was extracted with DCM (2 x 50 mL). Combined organics were washed with brine, dried over Na₂S0₄, filtered and evaporated to dryness to give the title compound (1.1 lg, 76percent) as a yellow oil. MS: 216.2 (M+H⁺).

76%

With triethylamine In dichloromethane at 0 - 20℃;

[A]
(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidine
To a solution of (S)-pyrrolidin-2-ylmethanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0° C. was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL).
The reaction mixture was then stirred at room temperature overnight and poured into NH₄Cl (20 mL).
The aqueous layer was extracted with DCM (2*50 mL).
Combined organics were washed with brine, dried over Na₂SO₄, filtered and evaporated to dryness to give the title compound (1.11 g, 76percent) as a yellow oil. MS: 216.2 (M+H⁺).

Reference： [1] Synlett, 2007, # 15, p. 2415 - 2419
[2] Patent: US2013/72679, 2013, A1, . Location in patent: Paragraph 0553; 0554
[3] Patent: WO2013/37779, 2013, A1, . Location in patent: Page/Page column 76; 77
[4] Patent: WO2013/79452, 2013, A1, . Location in patent: Page/Page column 237
[5] Patent: US2013/143863, 2013, A1, . Location in patent: Paragraph 1082; 1083; 1084
[6] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 2, p. 328 - 333

2
[ 128359-99-9 ]
[ 134756-75-5 ]

Reference： [1] Journal of the American Chemical Society, 1995, vol. 117, # 3, p. 891 - 899

3
[ 147-85-3 ]
[ 134756-75-5 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8625 - 8632

4
[ 18162-48-6 ]
[ 134756-75-5 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8625 - 8632

[ 134756-75-5 ] Synthesis Path-Downstream 1~32

1
[ 32315-10-9 ]
[ 134756-75-5 ]
[ 204580-49-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2007,vol. 55,p. 328 - 333

2
[ 134756-75-5 ]
(5S)-5-(tert-butyldimethylsilyloxymethyl)-1-pyrroline N-oxide [ No CAS ]
2-(tert-butyldimethylsilyloxymethyl)-1-pyrroline N-oxide [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 473 - 476

3
[ 18162-48-6 ]
[ 23356-96-9 ]
[ 134756-75-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In dichloromethane; at 20℃;	To a solution of (S)-pyrrolidin-2-yl-methanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 C. was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH4Cl (20 mL). The aqueous layer was extracted with DCM (2×50 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (1.11 g, 76%) as a yellow oil. MS: 216.2 (M+H+)
76%	With triethylamine; In dichloromethane; at 0 - 20℃;	Intermediate A-36-{5-[(S)-2-(tei"i-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-l-yl]-pyridin-3-yl}-l- methyl-3,4-dihydro-lH-quinolin-2-one [A] (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidineTo a solution of (S)-pyrrolidin-2-yl-methanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 C was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH4C1 (20 mL). The aqueous layer was extracted with DCM (2 x 50 mL). Combined organics were washed with brine, dried over Na2S04, filtered and evaporated to dryness to give the title compound (1.11 g, 76%) as a yellow oil. MS: 216.2 (M+H+).
76%	With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	To a solution of (S)-pyrrolidin-2-ylmethanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 C was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH4C1 (20 mL). The aqueous layer was extracted with DCM (2 x 50 mL). Combined organics were washed with brine, dried over Na2S04, filtered and evaporated to dryness to give the title compound (1.1 lg, 76%) as a yellow oil. MS: 216.2 (M+H+).

76%	With triethylamine; In dichloromethane; at 0 - 20℃;	[A] (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidine To a solution of (S)-pyrrolidin-2-ylmethanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 C. was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature overnight and poured into NH4Cl (20 mL). The aqueous layer was extracted with DCM (2*50 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (1.11 g, 76%) as a yellow oil. MS: 216.2 (M+H+).
	With 1H-imidazole; In tetrahydrofuran; at 20℃; for 2h;	[0869] To a mixture of L-prolinol (20 g, l97.73mmol), imidazole (4 g, 587.54mmol) in tetrahydrofuran (200 mL) was added Art-butyldimethylchlorosilane (45 g, 298.57mmol), the mixture was stirred for 2 hours at room temperature. Upon completion, the resulting solution was diluted with water, extracted with dichloromethane and the organic layers were combined. The organic layer was dried over anhydrous sodium sulfate and concentrated to afford crude product which directly used in the next step without purification. LC-MS: (ESI, m/z): 216.2 [M+H]+

Reference： [1]Synlett,2007,p. 2415 - 2419
[2]Patent: US2013/72679,2013,A1 .Location in patent: Paragraph 0553; 0554
[3]Patent: WO2013/37779,2013,A1 .Location in patent: Page/Page column 76; 77
[4]Patent: WO2013/79452,2013,A1 .Location in patent: Page/Page column 237
[5]Patent: US2013/143863,2013,A1 .Location in patent: Paragraph 1082; 1083; 1084
[6]Chemical and Pharmaceutical Bulletin,2007,vol. 55,p. 328 - 333
[7]Patent: WO2020/97537,2020,A2 .Location in patent: Paragraph 0869

4
[ 134756-75-5 ]
2-{{4-{[(S)-2-(hydroxymethyl)-1-pyrolidinyl]carbonyl}oxy}phenyl}thio}-7-isopropoxy-5,6-dimethoxy-4H-chromen-4-one [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2007,vol. 55,p. 328 - 333

5
[ 134756-75-5 ]
[ 204580-50-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2007,vol. 55,p. 328 - 333

6
[ 134756-75-5 ]
[ 862107-72-0 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2821 - 2824

7
[ 134756-75-5 ]
[ 862107-66-2 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2821 - 2824

8
[ 1622-32-8 ]
[ 134756-75-5 ]
[ 1039744-62-1 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2951 - 2954

9
[ 1037586-23-4 ]
[ 134756-75-5 ]
C₂₁H₃₅BrN₂O₂Si [ No CAS ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2905 - 2908

10
[ 134756-75-5 ]
4-(1-methyl-allyloxy)-3-oxo-butyric acid methyl ester [ No CAS ]
3-[2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-4-(1-methyl-allyloxy)-but-2-enoic acid methyl ester [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4224 - 4227

11
[ 134756-75-5 ]
4-allyloxy-3-oxo-butyric acid methyl ester [ No CAS ]
4-allyloxy-3-[2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-but-2-enoic acid methyl ester [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4224 - 4227

12
[ 134756-75-5 ]
[ 680973-45-9 ]
[ 1187661-41-1 ]
3-[2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-3-formyl-6-methyl-hept-5-enoic acid methyl ester [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4224 - 4227

13
[ 615-18-9 ]
[ 134756-75-5 ]
2-[(2S)-2-([(tert-butyl)(dimethyl)silyl]oxy}-methyl)pyrrolidin-1-yl]-1,3-benzoxazole [ No CAS ]