Ethanol → HCID 85888642, compound

HRID 372559Notes

Reaction equation

HRID 372559 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][CH:6]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:5]1.C(O)C>O>[OH:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][CH:6]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 54165967HCID 54165967, compound

Product 1

HCID 85888642HCID 85888642, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

5.75 g of sodium borohydride were slowly added to a solution of 11.5 g of the product of Step A in 11 5 ml of ethanol and 11.5 ml of water cooled to 10° C and the mixture was stirred for an hour at 20° C. The ethanol was evaporated and 100 ml of water were added. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness to obtain 11.35 g of 5ξ-hydroxy-7-(pyrrolidin-1-yl)-6,7,8,9-tetrahydro [5H] benzocycloheptene.

Workup

  1. customThe ethanol was evaporated
  2. addition100 ml of water were added
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e17584db9fca4bcba9336c8f2abf7240
Source dataset
uspto-grants-1978_05
Patent number
US04091115

Reaction notes

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