Ethyl Acetate → 6-(2,2-Dibromo-vinyl)-2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 1936016Notes

Reaction equation

HRID 1936016 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[CH:25]1([N:28]2[CH2:37][C:36]([CH3:39])([CH3:38])[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([CH:40]=O)[CH:34]=3)[CH2:29]2)[CH2:27][CH2:26]1.C(OCC)(=O)C>ClCCl.CCCCCC>[Br:21][C:20]([Br:24])=[CH:40][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[CH2:29][N:28]([CH:25]1[CH2:26][CH2:27]1)[CH2:37][C:36]2([CH3:39])[CH3:38]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 225689542-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carbaldehyde2×

Product 1

HCID 225689986-(2,2-Dibromo-vinyl)-2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

A stirred, cooled (ice-bath) solution of triphenyl phosphine (0.53 g, 2 mmol) in anhydrous dichloromethane was treated with carbon tetrabromide (0.35 g, 1 mmol) under argon. After 0.5 h, a solution of 2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxaldehyde (Intermediate 25, 0.13 g, 0.57 mmol) in dichloromethane (2 mL) was cannulated into the reaction mixture. After 1.5 h between 0° C. and 10° C., the reaction mixture was subjected to flash column chromatography over silica gel (230-400 mesh) using 3-5% ethyl acetate in hexane as the eluent to afford the title compound as a viscous, pale yellow oil (0.1 8 g, 82%).

Workup

  1. waitAfter 1.5 h between 0° C. and 10° C.

Sources & evidence

ORD record
ord-9366c4f0035d4aec849e32d4220c0c80
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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