Lithium borohydride → HCID 19742829, compound

HRID 2254637Notes

Reaction equation

HRID 2254637 reaction equation
[C:1]1([CH:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[CH:19]([C:20](OC)=[O:21])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[BH4-]>CCOCC>[C:32]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([N:10]2[CH:19]([CH2:20][OH:21])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)[CH2:11]2)=[O:9])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 10255071HCID 10255071, compound

Product 1

HCID 19742829HCID 19742829, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl 2-Diphenylacetyl-5-(p-methoxyphenyl)1,2,3,4-tetrahydroisoquinoline-3-carboxylate (0.47 g, 0.93 mmoles) was placed in 50 ml of ether. LiBH4 (0.10 g, 4.5 mmoles) was added. The reaction was stirred at room temperature for 3 days. The ether was evaporated. Methanol was carefully added to quench the LiBH4. The solution was diluted with water and then extracted with dichloromethane. The extracts were dried over MgSO4 and evaporated. The material was then chromatographed using 0-4% methanol in dichloromethane to give product (0.16 g, 0.33 mmoles) in 35% yield, m.p. 57°-63° C.

Workup

  1. customThe ether was evaporated
  2. additionMethanol was carefully added
  3. customto quench the LiBH4
  4. additionThe solution was diluted with water
  5. extractionextracted with dichloromethane
  6. dry with materialThe extracts were dried over MgSO4
  7. customevaporated
  8. customThe material was then chromatographed

Sources & evidence

ORD record
ord-f6ce64fadd5249568bc8a61bbb7f70f0
Source dataset
uspto-grants-1993_08
Patent number
US05236934

Reaction notes

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