Water → HCID 57905043, compound

HRID 1093064Notes

Reaction equation

HRID 1093064 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].O.[NH2:13][C:14]1([C:24]#[N:25])[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1.C([O-])([O-])=O.[Na+].[Na+].O>C(Cl)Cl.C(OCC)(=O)C.CCCCCC>[C:24]([C:14]1([NH:13][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:23][CH2:22][C:17]2([O:18][CH2:19][CH2:20][O:21]2)[CH2:16][CH2:15]1)#[N:25]

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 2735133Sodium Carbonate MonohydrateHCID 16789452HCID 16789452, compound

Product 1

HCID 57905043HCID 57905043, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Benzyl chloroformate (24.18 mL, 169.4 mmol) was added dropwise to a biphasic system of water (300 mL) and CH2Cl2 (150 mL) containing 8-amino-1,4-dioxaspiro[4.5]decane-8-carbonitrile (28 g, 154 mmol) and Na2CO3.H2O (22.9 g, 185 mmol) at 0° C. and stirred for 2 h. The mixture was then allowed to warm to room temperature and stirred for 18 h. The mixture was then diluted with CH2Cl2 (250 mL), washed with sat. NaHCO3 (200 mL), water (200 mL), followed by brine (100 mL) then dried (Na2SO4), filtered and concentrated to give a brown oil. Flash chromatography on silica gel (using a 5% to 40% ethyl acetate-hexane gradient) afforded the title compound as a white solid (45 g, 92% yield). 1H NMR (500 MHz, CDCl3) δ: 7.30-7.35 (m, 5H), 5.11 (s, 2H), 4.90 (brs, 1H), 3.86-3.96 (m, 4H), 2.36-2.41 (m, 2H), 1.84-2.01 (m, 4H), 1.73-1.76 (m, 2H). LCMS (M+H)=317.30.

Workup

  1. stirringstirred for 18 h
  2. washwashed with sat. NaHCO3 (200 mL), water (200 mL)
  3. dry with materialthen dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown oil

Sources & evidence

ORD record
ord-65164dcac3b142d2ad2d3945650381db
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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