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

HRID 1197810Notes

Reaction equation

HRID 1197810 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>[CH:2]1([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]2[CH2:14][CH2:15]2)[OH:12])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

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

Product 1

HCID 22850397tert-butyl [(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.83 g (8.77 mmol) of tert.-butyl [(1S,2R)-1-benzyl-2-(cyclopropylcarbonyl)-2-hydroxyethyl]carbamate are dissolved in methylene chloride (130 ml), acetic acid (3 ml) is added thereto and the mixture is then treated portionwise at 0°-10° with 332 mg (8.78 mmol) of sodium borohydride. The reaction solution is stirred at 5° for a further 2 hours and then partitioned between 2N sodium bicarbonate solution and methylene chloride. After the usual working-up of the organic phase the residue is crystallized from ether/hexane, whereby there are obtained 2.1 g (74%) of tert-butyl [(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamate, melting point 83°-85°.

Workup

  1. custompartitioned between 2N sodium bicarbonate solution and methylene chloride
  2. customis crystallized from ether/hexane, whereby there

Sources & evidence

ORD record
ord-7b5ccfa1b5d14e408b6a89ffe3fe2dc8
Source dataset
uspto-grants-1994_01
Patent number
US05278161

Reaction notes

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