Hydrochloric Acid → HCID 66905238, compound

HRID 1691418Notes

Reaction equation

HRID 1691418 reaction equation
Cl.[NH2:2][C@@H:3]1[C:12]([CH3:14])([CH3:13])[C:11]2[CH:10]=[C:9]([C:15]([NH2:17])=[O:16])[CH:8]=[CH:7][C:6]=2[CH2:5][C@H:4]1[O:18][CH3:19].C(N(CC)C(C)C)(C)C.[CH:29]([C@@H:31]1[CH2:35]OC(C)(C)[N:32]1C(OC(C)(C)C)=O)=[O:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCl.CO.CC(O)=O>[NH2:32][C@@H:31]([CH2:29][OH:30])[CH2:35][NH:2][C@@H:3]1[C:12]([CH3:14])([CH3:13])[C:11]2[CH:10]=[C:9]([C:15]([NH2:17])=[O:16])[CH:8]=[CH:7][C:6]=2[CH2:5][C@H:4]1[O:18][CH3:19]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 1798243-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-HCID 5049666Sodium triacetoxyborohydrideHCID 66674619HCID 66674619, compound

Product 1

HCID 66905238HCID 66905238, compoundYield 118.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of trans-7-amino-6-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide hydrochloride (229.3 mg, 0.81 mmol) in a mixture of dichloromethane (2.0 mL) and methanol (0.3 mL) was added N,N-diisopropyl-ethylamine (0.10 g, 0.80 mmol) followed by tert-butyl (4S)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (0.18 g, 0.80 mmol). Sodium triacetoxyborohydride (0.20 g, 0.97 mmol) was added and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated to dryness and dissolved in ethyl acetate (40 mL). The suspension was washed with saturated sodium bicarbonate (15 mL) and brine (15 mL), dried over sodium sulfate, filtered and concentrated to give a white foam. The white foam was treated with AcOH (1.0 mL) and 6N HCl (1.0 mL) at 70° C. for 1 h. The reaction mixture was concentrated, and evaporated with ethyl acetate (3×2 mL) to give the hydrochloride salt of the title compound as a dark greenish powder (304 mg, 96% yield). (m/z): [M+H]+ calcd for C17H27N3O3, 322.21; found, 322.2.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutiondissolved in ethyl acetate (40 mL)
  3. washThe suspension was washed with saturated sodium bicarbonate (15 mL) and brine (15 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a white foam
  8. concentrationThe reaction mixture was concentrated
  9. customevaporated with ethyl acetate (3×2 mL)

Sources & evidence

ORD record
ord-7059bb698ff645478579b5bed2ab73f9
Source dataset
uspto-grants-2012_04
Patent number
US08153686B2

Reaction notes

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