Ammonia → 9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane

HRID 1689301Notes

Reaction equation

HRID 1689301 reaction equation
N.[Si:2]([O:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([CH2:17][N:18]2[CH2:34][CH2:33][C:21]3([O:26][CH2:25][CH2:24][N:23](C(=O)C(F)(F)F)[CH2:22]3)[CH2:20][CH2:19]2)[S:15][CH:16]=1)([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]>CO>[Si:2]([O:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([CH2:17][N:18]2[CH2:34][CH2:33][C:21]3([O:26][CH2:25][CH2:24][NH:23][CH2:22]3)[CH2:20][CH2:19]2)[S:15][CH:16]=1)([C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 579892241-(9-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone

Product 1

HCID 579891139-((4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

‘880’ Aqueous ammonia (1.5 mL) was added to stirred solution of 1-(9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-2,2,2-trifluoroethanone (example 43, step a) (1.0 g) in methanol (5 mL). After 16 h the reaction mixture was evaporated to dryness. Acetonitrile was added, the solution evaporated to dryness in vacuo, and this process was repeated three times to give the subtitled compound as a white solid. Yield 0.78 g.

Workup

  1. customAfter 16 h the reaction mixture was evaporated to dryness
  2. additionAcetonitrile was added
  3. customthe solution evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a163493a41dc4fffb54d7a664f32c0b8
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…