Propylamine → HCID 67480475, compound

HRID 2273038Notes

Reaction equation

HRID 2273038 reaction equation
[CH2:1]([O:8][C@H:9]1[C@@H]2NC(=O)O[C@@H]2C[C@@H:11]([CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:10]1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.C[O+:42]([CH3:44])C.[CH2:45]([NH2:48])[CH2:46][CH3:47]>C(Cl)Cl>[CH2:1]([O:8][C@H:9]1[C@@H:45]2[N:48]=[C:44]([NH:48][CH2:45][CH2:46][CH3:47])[O:42][C@@H:46]2[CH2:47][C@@H:11]([CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:10]1[O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 67480268HCID 67480268, compound

Product 1

HCID 67480475HCID 67480475, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (3aR,4S,5S,6S,7aR)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)hexahydrobenzo[d]oxazol-2(3H)-one (400 mg, 0.85 mmol) and 4 Å MS (500 mg) in DCM (10 mL) was treated with trimethyloxonium tetrafluoroborate (650 mg, 4.39 mmol) for 16 h at room temperature, and followed by addition of propan-1-amine (3 mL) After stirred for additional 16 h at room temperature, the reaction mixture was poured into satd. aqueous NaHCO3 (50 mL), extracted with EtOAc (3×100 mL), washed with brine (30 mL), dried over anhydrous MgSO4, and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 3% MeOH and 1% ammonia (conc.) in EtOAc to give (3aR,4S,5S,6S,7aR)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-N-propyl-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazol-2-amine as yellow oil (300 mg, 69%). (ES, m/z) [M+H]+515.1; 1H NMR (300 MHz, CDCl3) δ 7.28-7.40 (m, 15H), 4.69-4.90 (m, 4H), 4.44-4.48 (m, 3H), 4.04-4.15 (m, 1H), 3.47-3.66 (m, 4H), 3.12-3.20 (m, 2H), 1.90-2.13 (m, 1H), 1.52-1.59 (m, 2H), 1.26-1.30 (m, 2H), 0.87-0.95 (t, J=7.2 Hz, 3H).

Workup

  1. additionthe reaction mixture was poured into satd
  2. extractionaqueous NaHCO3 (50 mL), extracted with EtOAc (3×100 mL)
  3. washwashed with brine (30 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under vacuum
  6. customto give a residue, which
  7. customwas purified by a silica gel column
  8. washeluted with 3% MeOH and 1% ammonia (conc.) in EtOAc

Sources & evidence

ORD record
ord-cc0d8f76767440d3bd011c4072f29e6e
Source dataset
uspto-grants-2015_09
Patent number
US09120781B2

Reaction notes

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