Hydrochloric Acid → HCID 58381236, compound

HRID 1025811Notes

Reaction equation

HRID 1025811 reaction equation
Cl.[CH3:2][C:3]([CH3:31])([CH3:30])[CH:4]([C:16]1[CH:29]=[CH:28][C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:18][CH:17]=1)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][N:14]=[N:13][N:12]=2)=[CH:7][CH:6]=1.[C:32]([N:39]1[CH2:44][CH2:43][CH:42]([CH2:45]O)[CH2:41][CH2:40]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(N1CCC(C=O)CC1)(OC(C)(C)C)=O>CCO.C(Cl)Cl>[C:35]([O:34][C:32]([N:39]1[CH2:44][CH2:43][CH:42]([CH2:45][N:14]2[N:13]=[N:12][C:11]([C:8]3[CH:7]=[CH:6][C:5]([CH:4]([C:16]4[CH:29]=[CH:28][C:19]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)=[CH:18][CH:17]=4)[C:3]([CH3:31])([CH3:30])[CH3:2])=[CH:10][CH:9]=3)=[N:15]2)[CH2:41][CH2:40]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178442176HCID 178442176, compound

Product 1

HCID 58381236HCID 58381236, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

HCl (1M solution in ethanol; slight excess) was added to a solution of 2d (42.0 mg, 0.102 mmol) in EtOH (1.0 mL) at room temperature. After ˜10 min, the resulting mixture was concentrated in vacuo to afford crude g. The residue was dissolved in DCM (1.5 mL), and to this solution was added N-Boc-4-piperidinemethanol (68.0 mg, 0.315 mmol), triphenylphosphine (132 mg, 0.505 mmol), and diethyl azodicarboxylate (80.0 μl, 0.511 mmol). After maintaining the reaction mixture at room temperature for 17 h, second portions of N-Boc-4-piperidinemethanal (68.0 mg, 0.315 mmol), triphenylphosphine (132 mg, 0.505 mmol), and diethyl azodicarboxylate (80.0 μl, 0.511 mmol) were added. The resulting solution was aged for another 5.5 μl, and then purified directly by flash chromatography on silica gel (gradient elution; 0%-50% EtOAc/hexanes as eluent) to afford 2h.

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. customto afford crude g
  3. custompurified directly by flash chromatography on silica gel (gradient elution; 0%-50% EtOAc/hexanes as eluent)
  4. customto afford 2h.

Sources & evidence

ORD record
ord-5495450c9cf1422db8ddf8052b24ae67
Source dataset
uspto-grants-2014_05
Patent number
US08729104B2

Reaction notes

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