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

HRID 1615124Notes

Reaction equation

HRID 1615124 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.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]([NH2:28])[CH3:27])=[CH:22][CH:21]=1>>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][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)[CH3:27])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 793467(S)-1-(4-Methoxyphenyl)ethylamineHCID 86668369(9-Hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-acetaldehyde

Product 1

HCID 679959809-{2-[(S)-1-(4-Methoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-olYield 45%

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-methoxy-phenyl)-ethylamine following a procedure analogous to that described in Step 3 of Intermediate 2. Yield: 45% of theory; LC (method 1): tR=1.44 min; Mass spectrum (ESI+): m/z=378 [M+H]+.

Sources & evidence

ORD record
ord-f80c05e53c10436fb2fcf856e92de745
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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