Pyridine → HCID 67285850, compound

HRID 2191370Notes

Reaction equation

HRID 2191370 reaction equation
[CH3:1][C:2]1([CH3:32])[O:6][C@@H:5]2[C:7]([CH2:11][O:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][C@H:9]([OH:10])[C@@H:4]2[O:3]1.N1C=CC=CC=1.Cl[C:40]([O:42][CH3:43])=[O:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:40](=[O:41])([O:42][CH3:43])[O:10][C@@H:9]1[C@H:4]2[C@H:5]([O:6][C:2]([CH3:32])([CH3:1])[O:3]2)[C:7]([CH2:11][O:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 10884464HCID 10884464, compound

Product 1

HCID 67285850HCID 67285850, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (1-1) (1.44 g, 3.36 mmol, 1.0 equiv) as dissolved in DCM (11.2 mL). Pyridine (0.489 mL, 6.05 mmol, 1.8 equiv) was added and the mixture stirred at 0° C. After 1 hour DMAP (164 mg, 1.34 mmol, 0.4 equiv) was added followed by methyl chloroformate (1.04 mL, 13.44 mmol, 4 equiv). The resulting mixture was stirred 12 h, and the temperature was allowed to slowly increase to 23° C. The reaction was partitioned between DCM and water, and the organic layer was separated and washed with water, dried (MgSO4), and concentrated to yield (3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methyl carbonate (1-2) as a white foam. 1H NMR (00 MHz, CDCl3) δ 7.21-7.47 (m, 15H), 6.03 (d, 1H, J=3.0 Hz), 5.32 (brm, 1H), 4.93 (t, 1H, J=9 Hz), 4.85 (d, 1H, J=10 Hz), 3.96 (d, 1H, J=24.5 Hz), 3.83 (s, 3H), 3.67 (d, 1H, J=24.5 Hz), 1.36 (s, 3H), 1.34 (s, 3H).

Workup

  1. stirringThe resulting mixture was stirred 12 h
  2. temperatureto slowly increase to 23° C
  3. customThe reaction was partitioned between DCM and water
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-21c35265c61042cda1d9b17c0bf34995
Source dataset
uspto-grants-2012_12
Patent number
US08329697B2

Reaction notes

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