Acetyl chloride → HCID 57659376, compound

HRID 1009818Notes

Reaction equation

HRID 1009818 reaction equation
[N:1]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:6][CH2:5][C:4]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C@@H:12]3[C@@H:8]([CH2:9][CH2:10][NH:11]3)[CH2:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>ClCCl>[C:33]([N:11]1[C@H:12]2[C@H:8]([CH2:7][C:4]3([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=42)[CH2:5][CH2:6][N:1]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:2][CH2:3]3)[CH2:9][CH2:10]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57659348HCID 57659348, compound

Product 1

HCID 57659376HCID 57659376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product of Step 2 (52 mg) was dissolved in dichloromethane (10 ml), treated with triethylamine (0.07 ml) and acetyl chloride (0.014 ml) for 1 h. The reaction mixture was diluted with dichloromethane, washed with water. The organic phase was concentrated to give (3aR,9bS)-tert-butyl 1-acetyl-1,2,3,3a,4,9b-hexahydrospiro[benzo[g]indole-5,4′-piperidine]-1′-carboxylate 14 (47 mg). LC-MS: m/e=329.6 (M+-tBu, 100%). Rt=3.21 min.

Workup

  1. washwashed with water
  2. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-f759fc6855cc41cf939e60e4089cad25
Source dataset
uspto-grants-2011_07
Patent number
US07973162B2

Reaction notes

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