(1S)-1-(2,5-dimethylphenyl)ethanamine → 9-{2-[(S)-1-(2,5-Dimethyl-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

HRID 1615132Notes

Reaction equation

HRID 1615132 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][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[C@@H:26]([NH2:28])[CH3:27]>>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[C@@H:26]([NH:28][CH2:16][CH2:15][C:2]1([OH:1])[CH2:3][CH2:4][C:5]2([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][O:10]2)[CH2:13][CH2:14]1)[CH3:27]

Participants

3

Reactant 2

HCID 7047659(1S)-1-(2,5-dimethylphenyl)ethanamineHCID 86668369(9-Hydroxy-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-acetaldehyde

Product 1

HCID 679958179-{2-[(S)-1-(2,5-Dimethyl-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-olYield 77%

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-(2,5-dimethyl-phenyl)-ethylamine following a procedure analogous to that described in Step 3 of Intermediate 2. Yield: 77% of theory; LC (method 5): tR=1.12 min; Mass spectrum (ESI+): m/z=376 [M+H]+.

Sources & evidence

ORD record
ord-5d07e28c7675417fb05c752d9d2ee4a5
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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