Triphosgene → 3-[(S)-1-(4-Fluoro-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

HRID 1615175Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]2([OH:26])[CH2:25][CH2:24][C:16]3([O:21]CC(C)(C)CO3)[CH2:15][CH2:14]2)[CH3:9])=[CH:4][CH:3]=1.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][C:13]3([CH2:14][CH2:15][C:16](=[O:21])[CH2:24][CH2:25]3)[O:26][C:28]2=[O:30])[CH3:9])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 94429Triphosgene

HCID 679954949-{2-[(S)-1-(4-Fluoro-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

Product 1

HCID 679961583-[(S)-1-(4-Fluoro-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dioneYield 50%

Procedure

The title compound is prepared from 9-{2-[(S)-1-(4-fluoro-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol and triphosgene following a procedure analogous to that described in Step 4 of Intermediate 2. Yield: 50% of theory; LC (method 5): tR=1.11 min; Mass spectrum (ESI+): m/z=306 [M+H]+.

Sources & evidence

ORD record: ord-e06d9ae592b54fbd883e32c9f81c99a6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765744B2

Reaction notes

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