Imidazole → HCID 86685349, compound

HRID 2273040Notes

Reaction equation

HRID 2273040 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:6]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:5]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][C@@H:3]1[OH:33].N1C=CN=C1.[C:39]([Si:43](Cl)([CH3:45])[CH3:44])([CH3:42])([CH3:41])[CH3:40]>C(Cl)Cl>[CH2:9]([O:8][C@H:7]1[C@H:6]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:5]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][C@H:3]([O:33][Si:43]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:45])[CH3:44])[C@@H:2]1[NH2:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86685348HCID 86685348, compound

Product 1

HCID 86685349HCID 86685349, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1S,2S,3R,4R,5R)-2-amino-3,4-bis(benzyloxy)-5-(benzyloxymethyl)cyclohexanol (1 g, 2.23 mmol) and imidazole (338 mg, 3.35 mmol) in DCM (20 mL) was treated with tert-butylchlorodimethylsilane (371 mg, 2.46 mmol) for 12 h at room temperature. The reaction was quenched by addition of satd. aqueous NaHCO3 (5 mL), and was extracted by DCM (2×10 mL). The organic layers were combined, dried over anhydrous MgSO4, and concentrated under vacuum to give a residue, which was purified by a silica gel column with 10% of MeOH in DCM to give (1R,2R,3R,4R,6S)-2,3-bis(benzyloxy)-4-(benzyloxymethyl)-6-(tertbutyldimethylsilyloxy)cyclohexanamine as a yellow oil (0.9 g, 68%). MS (ES, m/z): 562.3; 1H NMR (300 MHz, CDCl3) δ 7.24-7.37 (m, 15H), 4.80-4.95 (m, 2H), 4.55-4.71 (m, 2H), 4.40-4.51 (m, 2H), 4.05 (s, 1H), 3.62-3.67 (m, 1H), 3.44-3.50 (m, 3H), 2.43-2.46 (m, 1H), 2.15 (s, 1H), 1.82-1.85 (m, 1H), 1.52-1.59 (m, 1H), 0.92 (s, 9H), 0.11 (s, 3H), 0.08 (s, 3H).

Workup

  1. customThe reaction was quenched by addition of satd
  2. extractionaqueous NaHCO3 (5 mL), and was extracted by DCM (2×10 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by a silica gel column with 10% of MeOH in DCM

Sources & evidence

ORD record
ord-b5369171b9aa4394a3954d52bd653f62
Source dataset
uspto-grants-2015_09
Patent number
US09120781B2

Reaction notes

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