tert-Butyl isocyanate → HCID 89824960, compound

HRID 2273855Notes

Reaction equation

HRID 2273855 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[C:23]=[O:24]>O1CCCC1>[C:25]([NH:22][C:23](=[O:24])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 71580561HCID 71580561, compound

Product 1

HCID 89824960HCID 89824960, compoundYield 114%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(6-((tert-butyldimethylsilyl)oxy)hexyl)cyclohexanamine (330 mg, 1.05 mmol) in tetrahydrofuran (5 mL) at 0° C. was added 2-isocyanato-2-methylpropane (0.14 mL, 1.16 mmol). The mixture was stirred for 2 hours before it was quenched with methanol, and concentrated. Purification on silica gel with ethyl acetate: hexanes from 0:1 to 1:9 provided desired product as a clear oil (494.1 mg, 114%). 1H NMR (300 MHz, CDCl3): δ 4.11 (s, 1H), 3.99-3.84 (m, 1H), 3.56 (t, J=6.4 Hz, 2H), 2.92 (t, J=8.2 Hz, 2H), 1.80-0.94 (m, 18H), 0.85 (s, 9H), 0.05 (s, 6H).

Workup

  1. customwas quenched with methanol
  2. concentrationconcentrated
  3. customPurification on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-57ab5e0d696d4ec8ac86eb9b22f7ccc7
Source dataset
uspto-grants-2015_09
Patent number
US09126937B2

Reaction notes

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