HCID 117702502, compound → HCID 117717162, compound

HRID 1503263Notes

Reaction equation

HRID 1503263 reaction equation
[OH:1][CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH2:6]3)[CH2:4]1)[CH2:10]2.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[C:16]([O:15][C:14](=[O:20])[NH:13][C:5]12[CH2:11][CH:9]3[CH2:8][CH:7]([CH2:12][C:3]([CH:2]=[O:1])([CH2:10]3)[CH2:4]1)[CH2:6]2)([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 117702502HCID 117702502, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 117717162HCID 117717162, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(hydroxymethyl)-1-adamantylcarbamate (1.2 g, 4.3 mmol) in DCM (50 mL) was added PCC (1.4 g, 6.5 mmol) in portions under N2 atmosphere. After stirring at room temperature for two hours. the mixture was filtered through a pad of silica gel and the filtrate was concentrated under reduced pressure to give 1.1 g (92%) of the title compound, tert-butyl-3-formyl-1-adamantylcarbamate, as a brown oil, which was used in the next step without further purification. ESI-MS m/z: 224 (M-55)+.

Workup

  1. filtrationthe mixture was filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ba6ecdb1a9b1400a977253a3de4f6666
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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