Hydrochloric Acid → benzyl N-[(3R)-3,4-dihydroxybutyl]carbamate

HRID 1096296Notes

Reaction equation

HRID 1096296 reaction equation
C([O:3][C:4](=O)[C@H:5]([OH:19])[CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])C.[BH4-].[Na+].CO.Cl>CCO.C(Cl)Cl>[CH2:12]([O:11][C:9](=[O:10])[NH:8][CH2:7][CH2:6][C@@H:5]([OH:19])[CH2:4][OH:3])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 66782861(R)-4-Benzyloxycarbonylamino-2-hydroxy-butyric Acid ethyl ester

Product 1

HCID 12114860benzyl N-[(3R)-3,4-dihydroxybutyl]carbamateYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-4-benzyloxycarbonylamino-2-hydroxy-butyric acid ethyl ester (2.17 g, 7.71 mmol) in EtOH (6 mL) was added dropwise at <15° C. to a suspension of sodium borohydride (583 mg, 15.4 mmol) in EtOH (4 mL). The reaction mixture was stirred at RT for 16 h, then cooled to 5° C. and treated with MeOH (3 mL), then after 30 min acidified to pH 1-2 with conc. aq. HCl solution. The reaction mixture was stirred for 1 h, then diluted with CH2Cl2, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2/MeOH gradient) afforded the title compound (1.76 g, 96%). Light yellow solid, MS: 262.1 (M+Na)+.

Workup

  1. temperaturecooled to 5° C.
  2. stirringThe reaction mixture was stirred for 1 h
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7f8500bec68a4803a62c095d1ff9d4db
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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