Boron tribromide → (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1-(2-propenyl)-3a,8-dimethylpyrrolo[2,3-b]indol-5-ol

HRID 1736489Notes

Reaction equation

HRID 1736489 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[C@@H:13]3[N:14]([CH3:22])[C:15]4[C:20]([C@:12]3([CH3:23])[CH2:11][CH2:10]2)=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)C=CC=CC=1.COC1C=C2C(=CC=1)N(C)[C@H]1N(CC=C)CC[C@@]21C.B(Br)(Br)Br>C(Cl)(Cl)Cl>[CH2:8]([N:9]1[C@@H:13]2[N:14]([CH3:22])[C:15]3[C:20]([C@:12]2([CH3:23])[CH2:11][CH2:10]1)=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH:7]=[CH2:1]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 14349822(3aS-cis)-1,2,3,3a,8,8a-hexahydro-1-(2-phenylethyl)-3a, 8-dimethylpyrrolo[2,3-b]indol-5-olHCID 54079052(3aS-cis)-1,2,3,3a,8,8a-hexahydro-5-methoxy-1-(2-propenyl)-3a, 8-dimethylpyrrolo[2,3-b]indole

Product 1

HCID 57111400(3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1-(2-propenyl)-3a,8-dimethylpyrrolo[2,3-b]indol-5-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This compound is prepared in the same manner as the 1-(2-phenylethyl) derivative of Example 45 except that 2.58 g of (3aS-cis)-1,2,3,3a,8,8a-hexahydro-5-methoxy-1-(2-propenyl)-3a,8-dimethylpyrrolo[2,3-b]indole is reacted as a starting material with 10.1 g of boron tribromide in chloroform.

Sources & evidence

ORD record
ord-d400eb8e6130429aa9250d27aefb5730
Source dataset
uspto-grants-1996_07
Patent number
US05541216

Reaction notes

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