Acetic Acid → HCID 66783407, compound

HRID 1096274Notes

Reaction equation

HRID 1096274 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH:14]=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:17]1[C:19]2([CH2:24][CH2:23][NH:22][CH2:21][C@H:20]2[OH:25])[CH2:18]1.C(N(CC)CC)C.N1C=CC=CC=1.CC(O)=O>CCO.C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][N:22]1[CH2:23][CH2:24][C:19]2([CH2:17][CH2:18]2)[C@H:20]([OH:25])[CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 1049PyridineHCID 8471TriethylamineHCID 10398106Benzyl (3-Oxopropyl)carbamateHCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride

Product 1

HCID 66783407HCID 66783407, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(benzyloxycarbonyl)amino]-1-propanal (300 mg, 1.45 mmol) in EtOH (2 mL) and CH2Cl2 (2 mL) were added (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (284 mg, 1.74 mmol), triethylamine (176 mg, 1.74 mmol), borane pyridine complex solution (8 M in pyridine 0.34 mL, 3.2 mmol), and AcOH (400 mg, 6.66 mmol) at RT, then after 1 h the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; EtOAc-MeOH gradient) produced the title compound (404 mg, 88%). Colorless gum, MS: 319.1 (M+H)+.

Workup

  1. customafter 1 h the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1c88598aac004b83bcc4b1c45610dbec
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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