HCID 67408833, compound → HCID 44182352, compound

HRID 1913442Notes

Reaction equation

HRID 1913442 reaction equation
[CH2:1]1[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:6][CH2:5]2)[CH2:3][N:2]1C(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O.ClCCl>[CH2:3]1[C:4]2([CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9]2)[CH2:1][NH:2]1

Participants

4

Reactant 1

HCID 67408833HCID 67408833, compound

Product 1

HCID 44182352HCID 44182352, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

7-Benzyl 2-tert-butyl 2,7-diazaspiro[3.5]nonane-2,7-dicarboxylate (33.4 g, 92.8 mmol) was dissolved in a solution of TFA (50 mL) and dichloromethane (200 mL) and the reaction was stirred at room temperature overnight. The reaction was concentrated in vacuo and the residue was neutralized with saturated aqueous Na2CO3 (100 mL). The aqueous solution was washed with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4) and concentrated to give a yellow oil, which upon co-evaporation with dichloromethane provided benzyl 2,7-diazaspiro[3.5]nonane-7-carboxylate (SM-2a) as a white solid. (17.6 g, 73%). MS (ES+) 261.4 (M+H)+. 1H NMR (CDCl3) δ 1.67-1.89 (m, 4H), 2.86-3.18 (m, 2H), 3.40-3.64 (m, 7H), 5.12 (s, 2H), 7.30-7.39 (m, 5H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washThe aqueous solution was washed with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a yellow oil, which upon co-evaporation with dichloromethane

Sources & evidence

ORD record
ord-edccda6dbbab4bdd898e582e72c9d422
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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