HCID 21112788, compound → tert-Butyl [4-(aminomethyl)oxan-4-yl]carbamate

HRID 1504804Notes

Reaction equation

HRID 1504804 reaction equation
[C:1]([C:3]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]>[Ni].C(O)(C)C.N>[NH2:2][CH2:1][C:3]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

5

Reactant 1

HCID 21112788HCID 21112788, compound

Product 1

HCID 71744123tert-Butyl [4-(aminomethyl)oxan-4-yl]carbamate

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of tert-butyl (4-cyanotetrahydro-2H-pyran-4-yl)carbamate (59 g, 260 mmol) and Raney Nickel (25 g) in isopropanol and ammonia (700 mL) was stirred under a hydrogen atmosphere. After 36 hours, the solids were filtered and the filtrate was concentrated under reduced pressure. The residue was recrystallized from DCM (60 mL) to afford tert-butyl [4-(aminomethyl)tetrahydro-2H-pyran-4-yl]carbamate. MS ESI calc'd. for C11H23N2O3 [M+H]+ 231. found 231. 1H NMR (400 MHz, CDCl3) δ 4.42 (s, 1H), 3.77 (d, J=11.6 Hz, 2H), 3.66-3.60 (m, 2H), 2.94 (s, 2H), 1.97-1.94 (d, J=13.6 Hz, 2H), 1.57 (m, 2H), 1.44 (s, 9H), 1.28 (s, 2H).

Workup

  1. filtrationthe solids were filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from DCM (60 mL)

Sources & evidence

ORD record
ord-196a737674d34921aefd7cce60c0298c
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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