tert-Butyl 3-bromopropionate → HCID 66677999, compound

HRID 2410508Notes

Reaction equation

NC(=NO)C1C=CC(COCC(OC(C)(C)C)=O)=CC=1.[C:21]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][OH:27])#[N:22].Br[CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>>[C:21]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][O:27][CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])#[N:22]

Participants

Reactant 3

HCID 256128tert-Butyl 3-bromopropionate

HCID 27346773-(Hydroxymethyl)benzonitrile

HCID 76685345HCID 76685345, compound

Product 1

HCID 66677999HCID 66677999, compound

Procedure

The title compound was prepared according the procedure described for Intermediate 15 Step 1, but starting from 3-cyanobenzyl alcohol and tert-butyl 3-bromopropionate. It was isolated as a colorless oil (630 mg, 32%). 1H NMR (DMSO-d6, 300 MHz) δ 7.76 (m, 2H), 7.65 (m, 1H), 7.57 (m, 1H), 4.53 (brs, 2H), 3.64 (t, J=6.3 Hz, 2H), 2.49 (t, J=6.3 Hz, 2H), 1.40 (s, 9H). LC/MS (Method B) 262.2 (M+H)+. HPLC (Method A) Rt 4.75 min (Purity: 99.9%).

Sources & evidence

ORD record: ord-f798145af0a94092aa38145209f10984
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

Loading…