(1R)-1-(4-Bromophenyl)-2,2,2-trifluoroethan-1-ol → 10-[(R)-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one

HRID 2092676Notes

Reaction equation

HRID 2092676 reaction equation
[O:1]1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][NH:10][C:9]3=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Br[C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([OH:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1>>[F:25][C:24]([F:26])([F:27])[C@@H:23]([C:20]1[CH:21]=[CH:22][C:17]([N:10]2[CH2:11][CH2:12][C:8]3([CH2:14][CH2:15][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6][CH2:7]3)[C:9]2=[O:13])=[CH:18][CH:19]=1)[OH:28]

Participants

3

Reactant 2

HCID 12640349(1R)-1-(4-Bromophenyl)-2,2,2-trifluoroethan-1-olHCID 582301081,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

Product 1

HCID 5823010310-[(R)-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one

Procedure

The title compound was prepared in analogy to example 133, step 4 from 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (5.01 g) (described in example 133, step 3) and (1R)-1-(4-bromophenyl)-2,2,2-trifluoroethanol (9.07 g) (synthesis described in J. Org. Chem. 2009, 74, 1605-1610) as a white solid (4.9 g). MS (m/e): 386.1[MH+].

Sources & evidence

ORD record
ord-2393ce7672334ac1a9310a0e7199579e
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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