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Acetic Acid → tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamate

HRID 275628
Notes
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Reaction equation

HRID 275628 reaction equation
[CH2:1]([C@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:9]([C:11]([CH:13]1[CH2:15][CH2:14]1)=[O:12])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+]>C(Cl)Cl>[CH2:1]([C@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C@@H:9]([OH:10])[C@H:11]([CH:13]1[CH2:15][CH2:14]1)[OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86747482tert-butyl [(1S,2R)-1-benzyl-2-(cyclopropylcarbonyl)-2-hydroxyethyl]carbamate

Product 1

HCID 56984559tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamateYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

2.83 g (8.77 mmol) tert-butyl [(1S,2R)-1-benzyl-2-(cyclopropylcarbonyl)-2-hydroxyethyl]carbamate were dissolved in 130 ml of methylene chloride, 3 ml of acetic acid were added thereto and the mixture was finally treated portionwise at 0°-10° C. with 0.332 g (8.78 mmol) of sodium borohydride. The reaction solution was stirred at 50 for a further 2 hours and was then partitioned between 2N sodium hydrogen carbonate solution and methylene chloride. The organic phase was separated, washed with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and evaporated under reduced pressure. Crystallization of the residue from ether/hexane yielded 2.1 g of tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamate as colourless needles, m.p. 83-85°.

Workup

  1. customwas then partitioned between 2N sodium hydrogen carbonate solution and methylene chloride
  2. customThe organic phase was separated
  3. washwashed with water and with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customCrystallization of the residue from ether/hexane

Sources & evidence

ORD record
ord-851141cf5ff749208402cc1612f1fa39
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05393875

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes