HCID 68358820, compound → HCID 86707714, compound

HRID 1408978Notes

Reaction equation

HRID 1408978 reaction equation
[C:1]([C@@:3]1([CH3:21])[CH2:7][CH2:6][C@@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4]1([CH3:20])[CH3:19])#[N:2]>C1COCC1>[NH2:2][CH2:1][C@@:3]1([CH3:21])[CH2:7][CH2:6][C@@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:4]1([CH3:20])[CH3:19]

Participants

3

Reactant 1

HCID 68358820HCID 68358820, compound

Product 1

HCID 86707714HCID 86707714, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl ((1R,3S)-3-cyano-2,2,3-trimethylcyclopentyl)carbamate (1.53 g, 5.34 mmol) in THF (10.69 ml) at 0° C. was added a 2 M THF solution of borane-methyl sulfide complex (9.35 ml, 18.70 mmol). The reaction was allowed to warm to room temperature and stirring was continued for 14 hrs. The reaction was cooled to 0° C. and quenched with methanol (8 ml). The reaction solution was partitioned between ethyl acetate and 1.0 N NaOH. The organic extract was washed with brine, dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding benzyl ((1R,3S)-3-(aminomethyl)-2,2,3-trimethyl cyclopentyl)carbamate (1.39 g, 4.79 mmol, 90% yield) as a colorless oil. ESI-MS m/z 291.3 ([M+H]+).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with methanol (8 ml)
  3. customThe reaction solution was partitioned between ethyl acetate and 1.0 N NaOH
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53352d853e0f4d46bbc18cf014417d39
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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