Pyridine → HCID 59201347, compound

HRID 451756Notes

Reaction equation

HRID 451756 reaction equation
[NH2:1][C@@H:2]([C@H:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[OH:14])[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].N1C=CC=CC=1.[CH3:27][Si:28](Cl)([CH3:30])[CH3:29]>C1COCC1>[NH2:1][C@@H:2]([C@H:13]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[O:14][Si:28]([CH3:30])([CH3:29])[CH3:27])[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 59201362HCID 59201362, compound

Product 1

HCID 59201347HCID 59201347, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of crude tert-butyl (2R,3S)-2-amino-3-cyclohexyl-3-hydroxypropyl(methyl)carbamate (300 mg, 1.05 mmol) in anhydrous THF was added pyridine (846 μL, 10.50 mmol) and TMSCl (663 μL, 5.25 mmol). The mixture was heated to 60° C. and maintained for 20 min, then quenched with satd aq NaHCO3 (5 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried over NaSO4 and concentrated to afford tert-butyl (2R,3S)-2-amino-3-cyclohexyl-3-(trimethylsilyloxy)propyl(methyl)carbamate (350 mg, yield 93.1%). 1H NMR (400 MHz, MeOD): 0.13 (s, 9H), 0.80-1.40 (m, 6H), 1.40 (s, 9H), 1.50-2.10 (m, 5H), 2.90 (s, 3H), 3.15-3.50 (m, 4H). MS (E/Z): 359.0 (M+H+).

Workup

  1. temperaturemaintained for 20 min
  2. customquenched with satd aq NaHCO3 (5 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over NaSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ddd8cce37b664ec1861d9146f6964bb6
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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