Sodium borohydride → HCID 21459581, compound

HRID 1941015Notes

Reaction equation

HRID 1941015 reaction equation
[CH3:1][C:2]12[CH2:33][CH:5]([C:6]3([CH3:32])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([C:16]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[CH:24]=[C:23]([C:28]([O:30][CH3:31])=[O:29])[CH:22]=[CH:21]5)=[O:17])[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2.[BH4-].[Na+]>CO.O1CCCC1>[CH3:1][C:2]12[CH2:33][CH:5]([C:6]3([CH3:32])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([CH:16]([OH:17])[C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[CH:24]=[C:23]([C:28]([O:30][CH3:31])=[O:29])[CH:22]=[CH:21]5)[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21459578HCID 21459578, compound

Product 1

HCID 21459581HCID 21459581, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

944 mg (2.14 mmol) of the ester obtained in Example 3, dissolved in 30 ml of a methanol/tetrahydrofuran (1/1) mixture, were treated with 81 mg of sodium borohydride. The reaction mixture was stirred for 5 hours at room temperature. Evaporation was carried out to dryness, the residue was taken up in ether and this phase was washed to neutral pH. After drying and evaporating, 905 mg (96%) of the expected compound, melting at 140°-141° C., were isolated.

Workup

  1. customEvaporation
  2. washthis phase was washed to neutral pH
  3. customAfter drying
  4. customevaporating

Sources & evidence

ORD record
ord-eed553907aaa4149a7214d0be7d1f368
Source dataset
uspto-grants-1997_12
Patent number
US05702710

Reaction notes

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