Piperidine → HCID 69529238, compound

HRID 1796410Notes

Reaction equation

HRID 1796410 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([OH:23])=O)=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69529788HCID 69529788, compound

Product 1

HCID 69529238HCID 69529238, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.1 g (0.025 mole) of (2S)-2-tert-butoxycarbonylamino-7-hydroxycarbonylmethoxy-tetralin, 2.5 ml (0.025 mole) of piperidine, 11 g (0.025 mole) of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and 5.3 ml of triethylamine in 250 ml of dimethylformamide were mixed at ambient temperature for 6 hours. The solvent was evaporated off, the residue was taken up in water, it was extracted with ethyl acetate, the organic phase was washed with a saturated NaHCO3 solution, filtered over celite and washed with a dilute solution of acetic acid and with water. It was dried and the solvent was evaporated off under reduced pressure. The product was purified by crystallization from a 1:1 ethyl/hexane mixture. The product of the heading was obtained.

Workup

  1. customThe solvent was evaporated off
  2. extractionit was extracted with ethyl acetate
  3. washthe organic phase was washed with a saturated NaHCO3 solution
  4. filtrationfiltered over celite
  5. washwashed with a dilute solution of acetic acid and with water
  6. customIt was dried
  7. customthe solvent was evaporated off under reduced pressure
  8. customThe product was purified by crystallization from a 1:1 ethyl/hexane mixture
  9. customThe product of the heading was obtained

Sources & evidence

ORD record
ord-791de844654445e4ad4fcf0ac279dd80
Source dataset
uspto-grants-2006_04
Patent number
US07030160B2

Reaction notes

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