Diisobutylaluminum hydride → Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

HRID 1785794Notes

Reaction equation

HRID 1785794 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18](OC)=[O:19])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:19][CH2:18][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

Product 1

HCID 13969831Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 175A (1.22 g, 3.91 mmol) in toluene (10 mL) at −78° C. was treated with 1M DIBAL-H in toluene (8.6 mL), warmed to room temperature over 4 hours, diluted with ethyl acetate (100 mL), washed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 284 (M+H)+.

Workup

  1. washwashed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d538eb01bc4842b685617d6d5a94c62a
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

Loading…