tert-Butyl isocyanate → HCID 66745955, compound

HRID 1467204Notes

Reaction equation

HRID 1467204 reaction equation
[Cl-].[C:2]([C:4]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C@H:8]1[CH2:12][CH2:11][CH2:10][NH2+:9]1)#[N:3].[C:20]([N:24]=[C:25]=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[C:2]([C:4]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:25]([NH:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])#[N:3]

Participants

3

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 66746622HCID 66746622, compound

Product 1

HCID 66745955HCID 66745955, compoundYield 100%

Procedure

Prepared as in Example 165b from (R)-2-((2-cyano-3-nitrophenoxy)methyl)pyrrolidinium chloride (Example 176c) and tert-butyl isocyanate in 100% yield as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.s7 (s, 9H), 1.86 (m, 1H), 1.95 (m, 2H), 2.12 (m, 1H), 3.18 (m, 1H), 3.37 (m, 1H), 4.20 (m, 1H), 4.23 (dd, J=16.0, 6.3 Hz, 1H), 4.31 (dd, J=9.7, 2.7 Hz, 1H), 5.36 (s, 1H), 7.84 (dd, J=7.4, 0.9 Hz, 1H), 7.91 (m, 2H).

Sources & evidence

ORD record
ord-2d4a517cbf7444c98cb13184e8012bca
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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