| 99% |
With triethylamine In tetrahydrofuran |
|
| 99% |
With triethylamine In tetrahydrofuran at 0 - 20℃; |
31.A
To a solution of (lR, 2S)-l-amino-indan-2-ol (5.04 g, 33. 8 mmol) in THF (50 mL) cooled at 0°C were sequentially added triethylamine (5.65 MOL, 40. 6 mmol) and (Boc) 20 (7. 37 G, 33. 8 MMOL). The reaction mixture was stirred overnight at room temperature, quenched with H2O, and extracted with EtOAc (3 x 50 mL). The organic extracts were combined, washed with water and brine, and dried (MGSO4). Removal of the solvent gave the (1R, 2S)-(2-hydroyx-indan-1-yl)-carbamic acid tert- butyl ester (8.39 g, 99%) as a white solid, which was taken to the next step without purification. MS M/Z 250 [(M+H) +J. |
| 99% |
With triethylamine In tetrahydrofuran at 0 - 20℃; |
8.A
Part A ; To a solution of (1R, 2S)-L-AMINO-INDAN-2-OL (5.04 g, 33.8 mmol) in THF (50 mL) cooled at 0°C was added triethylamine (5.65 mL, 40.6 mmol) and (BOC) 20 (7.37 g, 33.8 mmol) sequentially. The reaction mixture was stirred overnight at room temperature, quenched with H2O, and extracted with EtOAc (3 x 50 mL). The organic extracts were combined, washed with water, brine, and dried (MgSO4). Removal of the solvent gave the desired product (1R, 2S)- (2-HYDROXY- INDAN-L-YL)-CARBAMIC acid tert-butyl ester (8.39 g, 99%) as a white solid that was taken to the next step without purification. |
| 98% |
In methanol at 20℃; |
7.1.1. (1R,2S)-1-(tertio-Butyloxycarbonylamino)indan-2-ol ((-)-7b)
To a solution of (+)-7a (400 mg, 2.68 mmol) in MeOH (10 mL) was added Boc2O (662 mg, 3.0 mmol, 1.1 equiv). After 3-5 h stirring at room temperature, the solvent was evaporated and the residue (0.9 g) recrystallised in cyclohexane to give pure (-)-7b (634 mg, 98%) as colorless crystals, mp = 77-79 °C [lit.24 for the (1S,2R)-enantiomer, mp 76.1-76.8 °C], inlMMLBox = -13 (c 1, CHCl3). 1H and 13C NMR (CDCl3) data were identical with those reported in the lit.24 |
| 96% |
With triethylamine In dichloromethane; ethyl acetate at 20℃; for 20h; |
41
Method #41 (1R,2S)-1-[(1,1-dimethylethoxy)carbonylamino]-2 hydroxyindan (1R,2S)-1-Amino-2-hydroxyindan (10.0 g, 67.1 mmol) was dissolved in dichloromethane (550 ml) and triethylamine (18.7 ml, 134.2 mmol). Di-tert-butyl dicarbonate (18.3 g, 83,9 mmol) in dichloromethane (50 ml) was added and the mixture stirred at room temperature for 20 hours then evaporated.ethyl acetate (200 ml) was added, the solution washed with water, dried over magnesium sulphate and evaporated.The crude product was purified by chromatography on silica with 4:1 iso-hexane:ethyl acetate as eluent to give the title compound as a white solid (16.1 g, 96%); NMR 1.42 (9H, s), 2.78 (1H, dd), 3.0 (1H, dd), 4.3-4.42 (1H, m), 4.78-4.9 (1H, m), 4.9-5.0 (1H, m), 6.3 (1H, d), 7.0-7.25 (4H, m). |
| 96% |
With triethylamine In dichloromethane at 20℃; for 20h; |
(LR, 2S)-1-AMINO-2, 3-dihydro-lH-inden-2-ol (CAS Reg. No. 136030-00-7; 10 g, 67.1 mmol) was dissolved in DCM (550 mL) and Et3N (18.7 mL, 134.2 MMOL). Di-tert-butyl dicarbonate (18.3 g, 83.9 mmol) in DCM (50 mL) was added and the mixture stirred at ambient temperature for 20 hours, anf then evaporated. EtOAc (200 mL) was added, the solution washed with water (200 mL), dried (MGS04) and the volatiles removed under reduced pressure. The crude product was purified by flash column chromatography (SI02, 4: 1, iso- hexane: EtOAc eluent) to provide the title compound (16.1 g, 96%) as a white solid. 'H NMR 8 : 1.42 (m, 9H), 2.78 (dd, 1H), 3.00 (dd, 1H), 4.36 (m, 1H), 4.84 (m, 1H), 4.95 (m, 1H), 6.3 (d, 1H), 7.13 (m, 4H). |
| 96% |
With triethylamine In dichloromethane at 18 - 25℃; for 20h; |
9
(1R, 2S)-1-Amino-2, 3-DIHYDRO-LH-INDEN-2-OL (CAS Reg. No. 136030-00-7; 10 g, 67.1 mmol) was dissolved in DCM (550 mL) and triethylamine (18.7 mL, 134.2 mmol). Di-tert-butyl dicarbonate (18.3 g, 83.9 mmol) in DCM (50 mL) was added and the mixture stirred at ambient temperature for 20 hours, and then evaporated. EtOAc (200 mL) was added, the solution washed with water (200 ML), dried (MGS04) and the volatiles removed under reduced pressure. The crude product was purified by flash column chromatography (SI02, 4: 1, iso-hexane : EtOAc eluent) to provide the title compound (16.1 g, 96%) as a white solid. H NMR 8 : 1.42 (m, 9H), 2.78 (dd, 1H), 3.00 (dd, 1H), 4.36 (m, 1H), 4.84 (m, 1H), 4.95 (m, 1H), 6.3 (d, 1H), 7.13 (m, 4H). |
| 96% |
Stage #1: (1R,2S)-(+)-cis-1-amino-2-indanol With triethylamine In dichloromethane at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: di-<i>tert</i>-butyl dicarbonate In dichloromethane at 0℃; Inert atmosphere; |
|
| 92% |
With anhydrous sodium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 0 - 20℃; for 3h; |
61.1 Step 1. tert-butyl ((lR,2S)-2-hydroxy-2,3- dihydro-lH-inden-l-yl)carbamate.
Step 1. tert-butyl ((lR,2S)-2-hydroxy-2,3- dihydro-lH-inden-l-yl)carbamate. To a stirring uspension of (1R, 2S)-(+)-cis-amino-2- indanol (115 mg, 0.77 mmol) and sodium carbonate (183 mg, 1.72 mmol) in THF (2.9 mL) and water (1.3 mL) was added a solution of di-tert-butyl dicarbonate (190 mg, 0.88 mmol) in THF (0.7 mL) and stirred at 0 °C for lh, then rt for 2h. The reaction mixture was diluted with water (50 mL), extracted with EtOAc (3 x 50 mL), and the combined organic phase was washed with brine and dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography using 25% EtOAc/Hexanes eluent to afford tert-butyl ((lR,2S)-2-hydroxy-2,3-dihydro-lH-inden-l- yl)carbamate as a white solid (117 mg, 92%). NMR (500MHz, CDC ) δ ppm 7.11 - 7.25 (m, 5H), 5.32 - 5.44 (m, 1H), 4.85 - 5.00 (m, 1H), 4.35 - 4.50 (m, 1H), 3.31 (bs, 1H), 2.99 (dd, J= 16.4, 4.6 Hz, 1H), 2.82 (dd, J= 10.3, 8.8 Hz, 1H), 1.47 (s, 9H). |
| 90% |
With triethylamine In dichloromethane at 20℃; for 20h; |
Intermediate 8: (1R, 2S)-L-[(L. L-DIMETHVLETHOXV) CARBONVLAMINOL-2 HVDROXVINDAN (1R, 2S)-1-Amino-2-hydroxyindan (12. 0g, 80. 5MMOL) was dissolved in DCM (500 ml) and triethylamine (22.4 ml, 161MMOL). Di-tert-butyl dicarbonate (22. 0g, 100MMOL) in DCM (50 ml) was added and the mixture stirred at room temperature for 20 hours then evaporated. EtOAc (200 ml) was added, the solution washed with water, dried over magnesium sulphate and evaporated. The crude product was purified by chromatography on silica with 4: 1 iso- hexane: EtOAc as eluent to give the title compound (17.9 g, 90%) as a white solid. HNMR 8 : 1.42 (s, 9H), 2.78 (dd, 1H), 3.00 (dd, 1H), 4.40 (m, 1H), 4.85 (M, 1H), 4.95 (m, 1H), 6.30 (d, 1H), 7.10 (m, 4H). |
| 90% |
With triethylamine In dichloromethane at 18 - 25℃; for 20h; |
10
(1R, 2S)-CIS-L-AMINO-2-HYDROXYINDAN (12.0 g, 80.5 mmol) was dissolved in DCM (500 mL) and triethylamine (22.4 mL, 161 mmol). Di-tert-butyl dicarbonate (22.0 g, 100 mmol) in DCM (50 mL) was added and the mixture stirred at room temperature for 20 h then evaporated. EtOAc (200 mL) was added, the solution washed with water, dried over magnesium sulphate and evaporated. The crude product was purified by chromatography on silica with 4: 1 iso-hexane: EtOAc as eluent to give the title compound (17.9 g, 90%) as a white solid. 1H NMR S : 1.42 (s, 9H), 2.78 (dd, 1H), 3.00 (dd, 1H), 4.40 (m, 1H), 4. 85 (m, 1H), 4.95 (m, 1H), 6. 30 (d, 1H), 7.10 (m, 4H). |
|
In methanol for 1h; Heating; |
|
|
With anhydrous sodium carbonate In tetrahydrofuran; lithium hydroxide monohydrate for 1.5h; |
Step (i): tert-butyl N- [(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-i-yij carbamate
Di-tert-butyl dicarbonate (3.42 mL, 14.75 mmoi) as a solution in THF (4 mL) was added to a stirred suspension of (1R,2S)-1-amino-2,3-dihydro-1H-inden-2-ol (2.0 g, 13.41 mmol) and Na2CO3 (2.84.g, 26.8 mmol) in THF (12 mL) and water (12 mL). After stirring for 1.5hours the reaction mixture was partitioned between water and EtOAc. The organics were separated, dried (phase separator) and concentrated in vacuo to afford the title compound. 1H NMR (300 MHz, DMSO-d6) ö ppm 1.45 (s, 9 H), 2.69 - 2.86 (m, 1 H), 2.94 - 3.08 (m, 1 H), 4.33 - 4.47 (m, 1 H), 4.82 - 5.04 (m, 2 H), 6.28 - 6.42 (m, 1 H), 7.12 - 7.24 (m, 4 H) |
|
With triethylamine In acetonitrile at 20℃; for 3h; |
Preparation of Compound S10
The Compound 10-1 was dissolved in acetonitrile, then triethylamine (2 eq) and BOC anhydride (1.05 eq) were added to the solution. After stirring at room temperature for 3 hours, the raw materials were completely reacted. Then the solvent was dried by rotary evaporation, and Compound 10-2 was obtained by silica gel column chromatography (DCM : MeOH = 30 : 1). |
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