Triphosgene → 3-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

HRID 1615174Notes

Reaction equation

HRID 1615174 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:12][CH2:13][CH2:14][C:15]2([OH:28])[CH2:27][CH2:26][C:18]3([O:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][O:19]3)[CH2:17][CH2:16]2)[CH:9]2[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH:9]2[CH2:10][CH2:11]2)[N:12]2[CH2:13][CH2:14][C:15]3([CH2:16][CH2:17][C:18](=[O:19])[CH2:26][CH2:27]3)[O:28][C:30]2=[O:32])=[CH:4][CH:3]=1.[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH:9]2[CH2:10][CH2:11]2)[N:12]2[CH2:13][CH2:14][C:15]3([CH2:27][CH2:26][C:18]4([O:19][CH2:20][C:21]([CH3:24])([CH3:25])[CH2:22][O:23]4)[CH2:17][CH2:16]3)[O:28][C:30]2=[O:32])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 679959259-(2-{[(S)-(4-Bromo-phenyl)-cyclopropyl-methyl]-amino}-ethyl)-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

Product 2

HCID 679957583-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-oneYield 37%HCID 679963643-[(S)-(4-Bromo-phenyl)-cyclopropyl-methyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Procedure

The title compound is prepared from 9-(2-{[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-amino}-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; besides the title compound the intermediate 3-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one (37% of theory) is also isolated. Yield: 25% of theory; LC (method 4): tR=1.59 min; Mass spectrum (ESI+): m/z=392/394 (Br) [M+H]+.

Sources & evidence

ORD record
ord-e9ccbf43c0b1466dace14a00f6fb86ac
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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