Water → HCID 13576833, compound

HRID 1905031Notes

Reaction equation

HRID 1905031 reaction equation
[C:1]([CH:4]1[CH:18]2[CH:7]([CH2:8][C:9]3[C:17]4[C:16]2=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:10]=3)[N:6]([CH3:28])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].O.ClCCl>C(O)C>[C:22]1([S:19]([N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[CH:18]5[CH:7]([CH2:8][C:9]([C:17]=34)=[CH:10]2)[N:6]([CH3:28])[CH2:5][CH:4]5[CH:1]([OH:3])[CH3:2])(=[O:21])=[O:20])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 13576795HCID 13576795, compound

Product 1

HCID 13576833HCID 13576833, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the 9-acetyl compound (Example 4) (0.10 g) in ethanol (2 cm3) was added sodium borohydride (0.0075 g) with visible reaction. After 2 hours reaction was indicated to be complete. Water (20 cm3) and dichloromethane (20 cm3) were added and the mixture partitioned, the separated aqueous layer was re-extracted with dichloromethane (20 cm3) to give, after evaporating under vacuum, a yellow-white solid.

Workup

  1. customwith visible reaction
  2. customAfter 2 hours reaction
  3. customthe mixture partitioned
  4. extractionthe separated aqueous layer was re-extracted with dichloromethane (20 cm3)
  5. customto give
  6. customafter evaporating under vacuum

Sources & evidence

ORD record
ord-a0033a6209714ea7acca61f47c3fd73f
Source dataset
uspto-grants-1989_06
Patent number
US04841056

Reaction notes

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