Ethyl trifluoroacetate → HCID 86628462, compound

HRID 2098523Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:13])[CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8].B.C1COCC1.[F:20][C:21]([F:28])([F:27])[C:22](OCC)=[O:23]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:13])[CH2:10][CH2:11][NH:12][C:22](=[O:23])[C:21]([F:28])([F:27])[F:20])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 3

HCID 9794Ethyl trifluoroacetate

HCID 2723981Borane;tetrahydrofuran

HCID 66629194HCID 66629194, compound

Product 1

HCID 86628462HCID 86628462, compound

Procedure

Reduction of 3-(3-bromo-4-fluorophenyl)-3-hydroxypropanenitrile with BH3-THF following the method used in Example 17, followed by protection of the amine with ethyl trifluoroacetate following the method used in Example 9 gave N-(3-(3-bromo-4-fluorophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide as a clear oil. Yield (4.3 g, 73%): 1H NMR (400 MHz, DMSO-d6) δ 9.31 (bs, 1H), 7.62 (dd, J=6.8, 2.0 Hz, 1H), 7.37-7.33 (m, 1H), 7.30 (t, J=8.8 Hz, 1H), 5.48 (d, J=4.4 Hz, 1H), 4.60-4.56 (m, 1H), 3.28-3.15 (m, 2H), 1.84-1.71 (m, 2H).

Sources & evidence

ORD record: ord-12cf1977417d479f8fe72d9813a86cdc
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450527B2

Reaction notes

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