Sodium borohydride → (2S,3R,4S)-2-[(tert-Butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

HRID 249405Notes

Reaction equation

HRID 249405 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:17]([OH:24])[C:18](=[O:23])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:17]([OH:24])[C@@H:18]([OH:23])[CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10427438HCID 10427438, compound

Product 1

HCID 9974740(2S,3R,4S)-2-[(tert-Butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptaneYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-3(R)-hydroxy-6-methylheptan4-one (200 mg, 0.586 mmol) in THF (10 mL) was added NaBH4 (22 mg, 0.586 mmol). After 2 hours, the solvent was evaporated and the residue was partitioned between ethyl acetate and brine. The organic phase was washed (brine), dried (MgSO4), filtered and evaporated. The residue was recrystallized from methylcyclohexane to give 76 mg (38%) of the desired product. M.p. 130°-131° C. The mother liquor was chromatographed (silica gel, ether/hexane) to afford 43 mg (21%) more.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed (brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-5e1ac6f3047142c092dd092b14b04614
Source dataset
uspto-grants-1993_05
Patent number
US05214129

Reaction notes

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