Hydrogen Bromide → (4aR,7aR)-Octahydro-1H-pyrrolo(3,4-b)pyridine

HRID 640676Notes

Reaction equation

C1(C)C=CC(S([N:10]2[CH2:18][C@@H:17]3[C@@H:12]([NH:13][CH2:14][CH2:15][CH2:16]3)[CH2:11]2)(=O)=O)=CC=1.Br.C(O)(=O)CC.C1(O)C=CC=CC=1>>[C@H:12]12[CH2:11][NH:10][CH2:18][C@H:17]1[CH2:16][CH2:15][CH2:14][NH:13]2

Participants

Reactant 4

HCID 260Hydrogen Bromide

HCID 996Phenol

HCID 1032Propionic Acid

HCID 44227364(R,R)-6-(toluene-4-sulfonyl)-octahydro-pyrrolo[3,4-b]pyridine

Product 1

HCID 1515156(4aR,7aR)-Octahydro-1H-pyrrolo(3,4-b)pyridineYield 84.4%

Procedure

The title compound (9.12 g) is prepared from mixture system of (R,R)-6-(toluene-4-sulfonyl)-octahydro-pyrrolo[3,4-b]pyridine (24.0 g), hydrobromic acid (48%, 156 ml), propionic acid (72 ml) and phenol (14.6 g) following the same procedure described in example 9. After conventional work up and distillation 3.4 g of oil is obtained (yield: 78.0%).

Workup

distillationAfter conventional work up and distillation 3.4 g of oil
customis obtained (yield: 78.0%)

Sources & evidence

ORD record: ord-88b39cc0ec8649c9be66aa8c615bfd7f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692015B2

Reaction notes

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