Methanol → phenylmethyl ({(3S,4R)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-4-hydroxy-3-piperidinyl}methyl)carbamate

HRID 657143Notes

Reaction equation

HRID 657143 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][NH:5][CH2:4][C@@H:3]1[CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CO.[F:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][C:29](=[O:36])[N:30]2[CH2:33][CH:34]=O)=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][C:29](=[O:36])[N:30]2[CH2:33][CH2:34][N:5]2[CH2:6][CH2:7][C@@H:2]([OH:1])[C@@H:3]([CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:4]2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 5049666Sodium triacetoxyborohydrideHCID 86635311(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehydeHCID 86635366Phenylmethyl {[(3R,4R)-4-hydroxy-3-piperidinyl]methyl}carbamate

Product 1

HCID 86635368phenylmethyl ({(3S,4R)-1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-4-hydroxy-3-piperidinyl}methyl)carbamateYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of phenylmethyl {[(3R,4R)-4-hydroxy-3-piperidinyl]methyl}carbamate (for a preparation see Example 135(f); 0.72 g; 2.72 mmol) in anhydrous DCM (10 mL) and anhydrous MeOH (2 mL) was added (7-fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde (for a preparation see Example 88(a)) (0.559 g; 2.72 mmol) and activated 4A sieves. The reaction was stirred under N2 for 18 h. The crude intermediate was treated with sodium triacetoxyborohydride (2.72 mmol; 577 mg) and stirred for 2 h. The product was obtained as a pale yellow oil after column:chromatography (90:10:DCM:MeOH) to yield 306 mg (25%) of the product as its free base.

Workup

  1. stirringstirred for 2 h
  2. customThe product was obtained as a pale yellow oil after column

Sources & evidence

ORD record
ord-99e6a6edfcb445f3b0cf30318fdaa84b
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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