Sodium borohydride → HCID 59591543, compound

HRID 1942578Notes

Reaction equation

HRID 1942578 reaction equation
[CH2:1]([N:7]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:8](=[O:31])[CH2:9][C:10](=[O:30])[CH2:11][CH:12]([OH:29])[CH2:13][C:14]1([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[S:19][CH2:18][CH2:17][CH2:16][S:15]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[BH4-].[Na+]>C(Cl)Cl.CO>[CH2:32]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8](=[O:31])[CH2:9][CH:10]([OH:30])[CH2:11][CH:12]([OH:29])[CH2:13][C:14]1([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[S:15][CH2:16][CH2:17][CH2:18][S:19]1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59591512HCID 59591512, compound

Product 1

HCID 59591543HCID 59591543, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the ketone 6e (242 mg, 0.44 mmol) in 6 mL of CH2Cl2 is added at 0° C. to a suspension of NaBH4 (50 mg, 1.32 mmol) in 9 mL of MeOH. After stiffing for 3 h at 0° C., the reaction medium is quenched by the addition of a saturated aqueous solution of NH4Cl. After dilution of the reaction medium in a CH2Cl2 and H2O mixture, it is extracted with CH2Cl2. The organic phases are then combined, dried over MgSO4, filtered and concentrated under vacuum. Purification is carried out on a silica column (cyclohexane/AcOEt 8:2) in order to produce the mixture of 4 non-separable diastereoisomers of the expected alcohol (173 mg, 0.03 mmol, 76%) in the form of a yellow oil.

Workup

  1. customthe reaction medium is quenched by the addition of a saturated aqueous solution of NH4Cl
  2. extractionAfter dilution of the reaction medium in a CH2Cl2 and H2O mixture, it is extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification
  7. customto produce

Sources & evidence

ORD record
ord-39b2635cf953449ca74dac4ac7889c45
Source dataset
uspto-grants-2013_03
Patent number
US08389569B2

Reaction notes

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