Methylamine → 9b-Allyl-8-benzyloxy-3a-hydroxy-3-methyl-2-oxo-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indole

HRID 224966Notes

Reaction equation

HRID 224966 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([CH2:25][CH:26]=[CH2:27])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:24])C.[CH3:29][NH2:30]>>[CH2:25]([C:6]12[C:15]3[CH:14]=[C:13]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]1([OH:24])[N:30]([CH3:29])[C:4](=[O:3])[CH2:5]2)[CH:26]=[CH2:27]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 54132972Ethyl-1-allyl-7-benzyloxy-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate

Product 1

HCID 233308199b-Allyl-8-benzyloxy-3a-hydroxy-3-methyl-2-oxo-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indole

Procedure

A mixture of 6.30 g (167 mmol) ethyl-1-allyl-7-benzyloxy-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate (IXc), 31.0 g methylamine and 200 ml 1:1 ethanol-dioxane was stirred at room temperature for 3 days. The reaction mixture was concentrated by evaporation of the solvent (35°-40° C.) to half the volume and diluted with 200 ml ether to provide a crystalline product which was collected to give 51.0 g (86%) Xc, m.p. 188°-190°; IR (Nujol), 3250, (broad), 1665, 1615, 1505 cm-1.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation of the solvent (35°-40° C.) to half the volume
  2. additiondiluted with 200 ml ether
  3. customto provide a crystalline product which
  4. customwas collected
  5. customto give 51.0 g (86%) Xc, m.p. 188°-190°

Sources & evidence

ORD record
ord-a62050af40214340bfeaf608ccda14c5
Source dataset
uspto-grants-1980_11
Patent number
US04234731

Reaction notes

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