Cyclopropylamine → HCID 39369612, compound

HRID 1525847Notes

Reaction equation

HRID 1525847 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>C(O)C>[CH:16]1([NH:19][CH2:2][C:3]2([OH:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Product 1

HCID 39369612HCID 39369612, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sealable reaction vessel was charged with 1,1-dimethylethyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (14.07 mmol), ethanol (70 mL) and cyclopropylamine (42.2 mmol). The vessel was purged with nitrogen, sealed and placed in a 75° C. oil bath for 20 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography (5% methanol in ethyl acetate). The appropriate fractions were concentrated under reduced pressure and dried to afford the title product (3.56 g, 94% yield) as a viscous colorless oil. MS(ES)+ m/e 271.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 4.20 (s, 1 H), 3.59 (d, J=12.6 Hz, 2 H), 3.05 (br. s., 2 H), 2.16-2.00 (m, 2 H), 1.49-1.31 (m, 14 H), 0.42-0.29 (m, 2 H), 0.24-0.13 (m, 2 H).

Workup

  1. customThe vessel was purged with nitrogen
  2. customsealed
  3. customplaced in a 75° C.
  4. customfor 20 h
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil was purified by silica gel chromatography (5% methanol in ethyl acetate)
  7. concentrationThe appropriate fractions were concentrated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-f430c511d1a1498bad5e3b135286b1fa
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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