Sodium borohydride → HCID 19864317, compound

HRID 1199920Notes

Reaction equation

HRID 1199920 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([CH:14]=[O:15])[S:13][C:7]=2[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5]1>C(O)C>[OH:15][CH2:14][C:12]1[S:13][C:7]2[CH:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:5][N:4]([CH3:3])[CH2:10][CH2:9][C:8]=2[CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19864322HCID 19864322, compound

Product 1

HCID 19864317HCID 19864317, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium borohydride (0.73 g) in ethanol (30 ml) was added dropwise to a stirred solution of 6-methyl-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine-2-carboxaldehyde (1.50 g) in ethanol (30 ml) cooled in an ice bath. After 30 minutes the solution was evaporated, the residue dissolved in water (100 ml) and extracted with dichloromethane (2×100 ml). The extracts were dried filtered and evaporated to a viscous oil. Crystallisation from cyclohexane (15 ml) gave the title product, m.p. 112°.

Workup

  1. temperaturecooled in an ice bath
  2. customAfter 30 minutes the solution was evaporated
  3. dissolutionthe residue dissolved in water (100 ml)
  4. extractionextracted with dichloromethane (2×100 ml)
  5. customThe extracts were dried
  6. filtrationfiltered
  7. customevaporated to a viscous oil
  8. customCrystallisation from cyclohexane (15 ml)

Sources & evidence

ORD record
ord-336d2296c8f9442d889827821992d38c
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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