Ammonia → HCID 58109245, compound

HRID 2037527Notes

Reaction equation

HRID 2037527 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]3[CH2:22][CH2:21][C@:20]([CH2:29][CH2:30][CH2:31][OH:32])([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:19][C:18]3=[O:33])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].[NH3:34].[BH4-].[Na+]>CCO.[NH4+].[OH-].C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[NH2:34][CH:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]3[CH2:22][CH2:21][C@:20]([CH2:29][CH2:30][CH2:31][OH:32])([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:19][C:18]3=[O:33])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 58109202HCID 58109202, compound

Product 1

HCID 58109245HCID 58109245, compoundYield 3%

Reagents, catalysts & solvents 3

HCID 178460666HCID 178460666, compoundCatalystHCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

(R)-3-((S)-1-(4-(5-acetylthiophen-2-yl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxa-zinan-2-one (40 mg, 0.086 mmol) and tetraisopropoxytitanium (49 mg, 0.17 mmol) are stirred overnight in the solution of NH3 in EtOH. To this solution/paste was added NaBH4 and stirring another 24 h. The reaction was diluted with NH4OH and stirred for 1 h. The mixture was filtered through celite and rinsed with EtOAc. Water and EtOAc were added and the organic layer was separated. The aq layer is extracted with EtOAc for three times. The combined organic layer was dried over Na2SO4, filtered and concentrated to afford (6R)-3-((1S)-1-(4-(5-(1-aminoethyl)thiophen-2-yl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (1.26 mg, 3%). LC-MS Method 2 tR=1.014, min, m/z=448.1; 1H NMR (CDCl3, 400 MHz): 1.33 (m, 1H), 1.47 (q, 6H), 1.90 (m, 2H), 2.13 (m, 1H), 2.22 (m, 2H), 2.82 (m, 1H), 3.50 (m, 2H), 4.33 (q, 1H), 5.58 (q, 1H), 6.81 (m, 3H), 6.98 (d, 1H), 7.25 (m, 7H).

Workup

  1. stirringstirred for 1 h
  2. filtrationThe mixture was filtered through celite
  3. washrinsed with EtOAc
  4. additionWater and EtOAc were added
  5. customthe organic layer was separated
  6. extractionThe aq layer is extracted with EtOAc for three times
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-84ee22f8ad9b41739e43166867bd6512
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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