(S)-1-(4-(Difluoromethoxy)phenyl)ethan-1-amine → 9-{2-[(S)-1-(4-Difluoromethoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

HRID 1615131Notes

Reaction equation

HRID 1615131 reaction equation
[OH:1][C:2]1([CH2:15][CH:16]=O)[CH2:14][CH2:13][C:5]2([O:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][O:6]2)[CH2:4][CH2:3]1.[F:18][CH:19]([F:30])[O:20][C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]([NH2:29])[CH3:28])=[CH:23][CH:22]=1>>[F:18][CH:19]([F:30])[O:20][C:21]1[CH:22]=[CH:23][C:24]([C@@H:27]([NH:29][CH2:16][CH2:15][C:2]2([OH:1])[CH2:14][CH2:13][C:5]3([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][O:10]3)[CH2:4][CH2:3]2)[CH3:28])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 42578528(S)-1-(4-(Difluoromethoxy)phenyl)ethan-1-amineHCID 86668369(9-Hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-acetaldehyde

Product 1

HCID 679958319-{2-[(S)-1-(4-Difluoromethoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-olYield 65%

Procedure

The title compound is prepared from (9-hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-acetaldehyde and (S)-1-(4-difluoromethoxy-phenyl)-ethylamine following a procedure analogous to that described in Step 3 of Intermediate 2. Yield: 65% of theory; LC (method 5): tR=1.02 min; Mass spectrum (ESI+): m/z=414 [M+H]+.

Sources & evidence

ORD record
ord-e1da50f8de2b4bea93f76a638d5efdd7
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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