Diethanolamine → HCID 12072785, compound

HRID 1018671Notes

Reaction equation

HRID 1018671 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]([C:21]([NH2:23])=[O:22])=[CH:11][C:12]3[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][O:14][C:13]=3[CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.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.N(CCO)CCO>C(Cl)Cl>[CH:1]1([CH2:7][O:8][C:9]2[C:10]([C:21]([NH2:23])=[O:22])=[CH:11][C:12]3[C@H:18]([OH:19])[CH2:17][CH2:16][CH2:15][O:14][C:13]=3[CH:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 10663295HCID 10663295, compoundHCID 13515837Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)borane

Product 1

HCID 12072785HCID 12072785, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-12 °C

Procedure

To 8-cyclohexylmethoxy-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-7carboxylic acid amide (4.0 g, 13.3 mmol) suspended in CH2Cl2 (25 mL) at 42° C. was added (+)-DIP-Chloride (25 mL of CH2Cl2). The mixture was stirred at −12° C. for 18 h, concentrated, diluted with Et2O (200 mL) and treated with diethanolamine (5.1 mL, 53.1 mmol). After stirring for 2.5 h, the formed solids were filtered and washed with Et2O. The filtrate was concentrated, and the residue purified by silica gel column chomatography (5% MeOH/CH2Cl2) to a white solid (3.2 g, 80%). m.p. 164-165° C. Optical purity determined by Mosher Amide formation, 71% e.e.

Workup

  1. concentrationconcentrated
  2. additiondiluted with Et2O (200 mL)
  3. stirringAfter stirring for 2.5 h
  4. filtrationthe formed solids were filtered
  5. washwashed with Et2O
  6. concentrationThe filtrate was concentrated
  7. customthe residue purified by silica gel column chomatography (5% MeOH/CH2Cl2) to a white solid (3.2 g, 80%)

Sources & evidence

ORD record
ord-4747776f1bec4d57851a24c034c7b067
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

Loading…