Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)borane → HCID 58997974, compound

HRID 1592828Notes

Reaction equation

HRID 1592828 reaction equation
B(Cl)([C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[CH2:23]([N:30]1[CH2:35][CH2:34][O:33][C@@H:32]([C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:37])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:38]1([C@H:36]([C@@H:32]2[O:33][CH2:34][CH2:35][N:30]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:31]2)[OH:37])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

3

Reactant 2

HCID 13515837Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)boraneHCID 58610174[(2R)-4-Benzylmorpholin-2-yl](phenyl)methanone

Product 1

HCID 58997974HCID 58997974, compound

Procedure

To a stirred solution of (+)-DIP chloride (49.6 g, 155 mmol) in dry TBF (150 ml) under nitrogen was added (2R)-(4-benzyl-morpholin-2-yl)-phenyl-methanone (16.54 g, 58.89 mmol) in one portion. The reaction mixture was stirred at room temperature for 18 hours. The mixture was evaporated in vacuo and the crude oil taken up in methanol and absorbed onto 250 g SCX-2 ion exchange resin. After elution of borane residues with methanol the product was eluted with 2M ammonia in methanol. Removal of solvent in vacuo yielded the product as yellow oil. (11.23 g, 67%); MW 283.37; C18H21NO2; 1H NMR (CDCl3): 7.32-7.45 (10H, m), 4.67 (1H, d, 7.3 Hz), 4.03 (1H, dt, 11.4 Hz, 2.7 H), 3.86-3.73 (2H, m), 3.64 (1H, d, 13.2 Hz), 3.39 (1H, d, 13.2 Hz), 3.30 (1H, br. s), 2.68 (1H, d, 12.7 Hz), 2.56 (1H, d, 10.9 Hz), 2.28-2.15 (2H, m); LCMS: m/z 284 [M+H]+ @ Rt 0.95 min.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customabsorbed onto 250 g SCX-2 ion exchange resin
  3. washAfter elution of borane residues with methanol the product
  4. washwas eluted with 2M ammonia in methanol
  5. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-f0342efdafef446283a5a740fad95978
Source dataset
uspto-grants-2007_11
Patent number
US07294623B2

Reaction notes

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