[ CAS No. 438049-91-3 ] {[proInfo.proName]}

Name: 438049-91-3|(3R,5R)-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate|97%
Brand: Ambeed
SKU: A135685
Price: 63.0 USD
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Quality Control of [ 438049-91-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 438049-91-3 ]

SDS Specification

Alternatived Products of [ 438049-91-3 ]

Product Details of [ 438049-91-3 ]

CAS No. :	438049-91-3	MDL No. :	MFCD08686695
Formula :	C₁₁H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NUZXPHIQZUYMOR-RKDXNWHRSA-N
M.W :	214.30	Pubchem ID :	51670829
Synonyms :

Calculated chemistry of [ 438049-91-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	68.12
TPSA :	41.57 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) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.9
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	0.84
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	0.69
Consensus Log Po/w :	1.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.8
Solubility :	3.38 mg/ml ; 0.0158 mol/l
Class :	Very soluble
Log S (Ali) :	-1.79
Solubility :	3.44 mg/ml ; 0.0161 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.6
Solubility :	5.42 mg/ml ; 0.0253 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.09

Safety of [ 438049-91-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 438049-91-3 ]

* 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 [ 438049-91-3 ]
Downstream synthetic route of [ 438049-91-3 ]

[ 438049-91-3 ] Synthesis Path-Upstream 1~1

1
[ 24424-99-5 ]
[ 438049-91-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine In dichloromethane at 20℃; for 48 h;	Step A: To a solution of (2R,6R)-2,6-dimethylpiperazine dihydrochloride (1.60 g, 8.55 mmol), in CH₂Cl₂(15 mL) at room temperature was added triethylamine (2.50 mL, 17.95 mmol) followed by di-tert butyldicarbonate (2.05 g, 9.40 mmol) and the reaction mixture was allowed to stir at room temperature 48 h. The reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO₃(20 mL). The aqueous phase was further extracted with EtOAc (2.x.20 mL). The combined organic phase was washed with brine (20 mL) and dried (Na₂SO₄). The crude product was purified by column chromatography (silica gel, 3 to 10percent CH₃OH in CH₂Cl₂) to afford (3R,5R)-tert-butyl 3,5-dimethylpiperazine-1-carboxylate (1.17 g, 64percent) as a clear oil. ¹H NMR and MS consistent.

Reference： [1] Patent: US2008/255114, 2008, A1, . Location in patent: Page/Page column 23

[ 438049-91-3 ] Synthesis Path-Downstream 1~12

1
[ 24424-99-5 ]
(2R,6R)-2,6-dimethylpiperazine dihydrochloride [ No CAS ]
[ 438049-91-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine; In dichloromethane; at 20℃; for 48h;	Step A: To a solution of (2R,6R)-2,6-dimethylpiperazine dihydrochloride (1.60 g, 8.55 mmol), in CH2Cl2 (15 mL) at room temperature was added triethylamine (2.50 mL, 17.95 mmol) followed by di-tert butyldicarbonate (2.05 g, 9.40 mmol) and the reaction mixture was allowed to stir at room temperature 48 h. The reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 (20 mL). The aqueous phase was further extracted with EtOAc (2×20 mL). The combined organic phase was washed with brine (20 mL) and dried (Na2SO4). The crude product was purified by column chromatography (silica gel, 3 to 10% CH3OH in CH2Cl2) to afford (3R,5R)-tert-butyl 3,5-dimethylpiperazine-1-carboxylate (1.17 g, 64%) as a clear oil. 1H NMR and MS consistent.

Reference： [1]Patent: US2008/255114,2008,A1 .Location in patent: Page/Page column 23

2
[ 438049-91-3 ]
(3R,5S)-tert-butyl 3,5-dimethyl-4-(3-((methylsulfonyl)oxy)propyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/191172,2016,A1

3
[ 438049-91-3 ]
[ 627-18-9 ]
(3R,5S)-tert-butyl 4-(3-hydroxypropyl)-3,5-dimethylpiperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 2h;Microwave irradiation;	A mixture of (3S,5R)-tert-butyl 3,5-dimethylpiperazine-l-carboxylate (2.14g, 10.0 mmol), 3-bromopropan-l-ol (2.76 g, 20 mmol) and K2C03(2.76 g, 20 mmol) in DMF (5.0 mL) was heated to 90C for 2 h in a microwave. The reaction mixture was poured into water (30 mL) and extracted with EtOAc. The organic phase was separated, dried and concentrated. The residue was purified by chromatography (DCM:MeOH=30: 1) to provide (3R,5S)-tert-butyl 4-(3- hydroxypropyl)-3,5-dimethylpiperazine-l-carboxylate as a yellow liquid (2.14g, 50%).

Reference： [1]Patent: WO2016/191172,2016,A1 .Location in patent: Page/Page column 61-62

4
[ 6704-31-0 ]
[ 438049-91-3 ]
tert-butyl (3R,5S)-3,5-dimethyl-4-(oxetan-3-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture containing <strong>[438049-91-3](3S,5R)-tert-butyl 3,5-dimethylpiperazine-1-carboxylate</strong> (500 mg, 2.33 mmol) and oxetan-3-one (0.40 g, 5.6 mmol) in dichloroethane (10 mL) was treated with aceticacid (0.20 mL, 3.5 mmol) and stirred at 50C for two hours, then cooled to room temperature. Sodium triacetoxyborohydride (1.0 g, 4.7 mmol) was added and the reaction mixture stirred at room temperature for 15 h. The crude reaction mixture was diluted with DCM (50 mL) and washed with water (3 x 50 mL). The organic layer was dried over Na2SO4, filtered and concentrated to provide tert-butyl (3R,5S)-3 ,5 -dimethyl-4-(oxetan-3 -yl)piperazine- 1 -carboxylate.

Reference： [1]Patent: WO2019/74809,2019,A1 .Location in patent: Page/Page column 33; 34

5
[ 438049-91-3 ]
C₉H₁₈N₂O*C₂HF₃O₂ [ No CAS ]

Reference： [1]Patent: WO2019/74809,2019,A1

6
[ 438049-91-3 ]
[ 29578-39-0 ]
tert-butyl (3R,5R)-4-(3-fluoro-5-methoxyphenyl)-3,5-dimethylpiperazine-1-carboxylate [ No CAS ]