Citric Acid → tert-Butyl-7-(1-cyano-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2167441Notes

Reaction equation

HRID 2167441 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12](/[C:18](/[C:26]#[N:27])=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([C:26]#[N:27])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 66978138(Z)-tert-Butyl-7-(1-cyano-2-phenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 66978151tert-Butyl-7-(1-cyano-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 0.178 mmol of (Z)-tert-butyl-7-(1-cyano-2-phenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 2 ml ethanol were added at 0° C. 0.178 mmol of sodium borohydride. The mixture was allowed to warm to room temperature and stirred for 3 d. The mixture was poured on ice water and citric acid (5%) was added until acidic. The aqueous phase was extracted with EtOAc. The combined organic phase was washed with brine, dried over MgSO4, and filtered. Evaporation of the solvent gave 61.2 mg (95%) of a crude slightly yellow oil, that was directly submitted to Boc deprotection.

Workup

  1. additionwere added at 0° C
  2. additionwas added until acidic
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of the solvent
  8. customgave 61.2 mg (95%) of a crude slightly yellow oil, that

Sources & evidence

ORD record
ord-ececcb87103a49a7acc07a05b6127085
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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