HCID 86731701, compound → HCID 86731700, compound

HRID 1504813Notes

Reaction equation

HRID 1504813 reaction equation
[C:1]([C:3]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[CH2:5][CH2:4]1)#[N:2]>[Ni]>[NH2:2][CH2:1][C:3]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 86731701HCID 86731701, compound

Product 1

HCID 86731700HCID 86731700, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Methanol (800 mL) was bubbled with ammonia gas. After 1 hour, Raney Nickel (50 g) and tert-butyl (4-cyano-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbamate (70 g, 255 mmol) were added. The reaction mixture was stirred under a hydrogen atmosphere. After 16 hours, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to afford tert-butyl [4-(aminomethyl)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]carbamate. MS ESI calc'd. for C11H23N2O4S [M+H]+ 279. found 279. 1H NMR (400 MHz, CDCl3) δ 4.54 (s, 1H), 3.25-3.15 (m, 2H), 3.00-2.90 (m, 4H), 2.64-2.60 (m, 2H), 2.13-2.06 (m, 2H), 1.78 (bs, 2H), 1.45 (s, 9H).

Workup

  1. customMethanol (800 mL) was bubbled with ammonia gas
  2. waitAfter 16 hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc94c1980f854b8c942cbbe99c8ff291
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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