tert-Butyl carbamate → HCID 3698650, compound

HRID 75686Notes

Reaction equation

HRID 75686 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]([OH:16])[CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](=[O:24])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[NH2:18]>>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]([OH:16])[CH2:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[O:16]=[C:10]1[CH:9]2[CH2:15][CH2:14][CH:12]([CH2:13][N:18]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[CH2:11]1

Participants

4

Reactant 2

HCID 77922tert-Butyl carbamateHCID 3698650HCID 3698650, compound

Product 2

HCID 3698650HCID 3698650, compoundHCID 672340172-Boc-2-azabicyclo[2.2.2]octane-6-one

Procedure

2-benzyl-2-azabicyclo[2.2.2]octan-6-ol is prepared using a method analogous to that described in U.S. Pat. No. 5,147,873. 2-benzyl-2-azabicyclo[2.2.2]octan-6-ol is debenzylated and subsequently protected as the tert-butyl carbamate using procedures analogous to those described in Example 1. Oxidation of the resulting intermediate alcohol using the Swern protocol affords the title product.

Sources & evidence

ORD record
ord-0454cfcfff4f4525ae5c8632df657eb0
Source dataset
uspto-grants-2014_09
Patent number
US08835457B2

Reaction notes

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